Hydrochloric Acid → 4-(1H-1,2,4-Triazol-1-ylmethyl)benzenamine hydrochloride

HRID 487981Notes

Reaction equation

HRID 487981 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:6][CH:5]=1)([O-])=O.[ClH:16]>C(O)C.C(OCC)(=O)C.O.[Pd]>[ClH:16].[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:6][CH:5]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 64820001-(4-Nitrobenzyl)-1H-1,2,4-triazole

Product 1

HCID 117012794-(1H-1,2,4-Triazol-1-ylmethyl)benzenamine hydrochlorideYield 100%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4-nitrophenyl)methyl-1,2,4-triazole (10.0 g, 49 mmol) in ethanol (50 ml), ethyl acetate (50 ml), 5N HCl (10 ml) and water (10 ml) was hydrogenated over 10% Pd/C (1.0 g) at 40 p.s.i., in a Parr apparatus, until an uptake of 188 p.s.i., had been observed (approx 10 mins). The catalyst was removed by filtration through hyflo and the solvent removed under vacuum. The residue was azeotroped with ethanol (×2) to give the titleamine hydrochloride (10.6 g, 100%). δ (360 MHz, D2O) 5.53 (2H, s, CH2), 7.37-7.48 (4H, m, Ar-H), 8.12 (1H, s, Ar-H), 8.66 (1H, s, Ar-H).

Workup

  1. custom(approx 10 mins)
  2. customThe catalyst was removed by filtration through hyflo
  3. customthe solvent removed under vacuum
  4. customThe residue was azeotroped with ethanol (×2)

Sources & evidence

ORD record
ord-dd549791586d4bd191de735d3f72b23d
Source dataset
uspto-grants-1994_03
Patent number
US05298520

Reaction notes

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